Wayside School Fan Fiction

Wayside School Fan Fiction
_____W A Y S I D E - S C H O O L - F A N - F I C T I O N_____

Saturday, February 14, 2026

HAIR DRIVE

The following story focuses on Joe, the main character in Chapter 3 of Sideways Stories from Wayside School. Before we dive into the fan‑fiction, let’s take a quick look at what the third chapter is about.


CHAPTER 3. JOE — SUMMARY

There seems to be a strange connection between Joe’s inability to count and his curly hair. When Mrs. Jewls discovers that Joe doesn’t know how many hairs he has, or even how to count properly, she keeps him in during recess to practice. But by the end of recess, Joe still can’t count correctly, which makes him sad. Mrs. Jewls reassures him that one day he’ll simply wake up and know how to count. The chapter ends happily: the next morning, Joe suddenly becomes good at math and is finally able to count all his curly hairs.




Joe had curly hair. All the other boys in Mrs. Jewls's class had straight hair. A couple of girls had wavy or curly hair too, but Joe was the only boy whose hair looked like an explosion in the slinky factory.

Every morning, Joe spent more than half an hour trying to tame it. He stood in front of the tall mirror on his closet door, armed with a big comb and two hairbrushes, hoping to look neat and tidy like his best friend John. But no matter how hard he tried, his hair always ended up looking like the back of a stray sheep.

When Joe got to school, he met John on the stairs.

"Hi, Joe," John said. "Did you comb your hair this morning?"

Joe tried to run a hand through his curls. It got stuck in a knot right on his forehead. "I woke up late today," he lied. "I barely had time for breakfast."

At lunchtime, Joe headed to the cafeteria. They had just finished math, and his brain was still a jumble of numbers and fractions.

"Hey, Joe!" John called. He was already sitting with Myron and Todd. "Over here!"

Joe sat down and opened his lunch bag. "I brought my own lunch," he said. "I just came for a glass of milk from Miss Mush."

"Me too," John laughed. 

Todd pointed at Louis, who was eating at a nearby table. "Louis is the only one eating Miss Mush's special today. He's already finished a whole bottle of ketchup."

Louis waved at them. "Boys, how would you like a free haircut?"

"Are you a barber too, Louis?" Myron asked.

Louis shook his head. "There's a barber downstairs giving free haircuts today. I"m trying to finish lunch fast so I can get mine."

Joe didn't feel excited. Barbers always had trouble cutting his hair. But John, Todd, and Myron were curious. They gulped down their food and ran downstairs. Joe followed them quietly.

Outside, behind the basketball court, they found a colorful pickup truck with a small trailer attached. A big sign read:

HAIR DRIVE - THE NEWEST BARBERSHOP IN TOWN.

FREE HAIRCUTS TODAY!

Just then, Louis stepped out of the trailer. he looked so neat and handsome that the boys almost didn't recognize him.

"Hey, Louis," Todd called. "You look like you're going to your own wedding!"

Louis grinned, ran a hand through his hair and hurried off to fetch the green and red balls.

"Should we get our hair cut?" John asked.

"I don't know," Joe said. "My hair doesn't work in regular barbershops."

"I just want a trim," Myron said. "My hair already looks perfect."

He was right.


"Welcome, boys!" the barber said. He was tall, with a sharp haircut and a mustache twice as perfect as Louis's. "Who's first?"

"Me!" Todd shouted.

Todd and Myron were done quickly because they only needed a little trimming. When John sat in the chair, the barber studied his hair for a minute.

"What if we switch your part to the other side?" he suggested. "It'll make your look ten years younger."

"I don't want to look like a baby!" John protested.

"You know what I mean," the barber chuckled.

A few snips later, John looked like he had stepped out of a gift box.

"Thank you!" he said, admiring himself in the mirror.

"Now it's your turn," the barber said, turning to Joe.

Joe shook his head. "I can't. My hair is curly. It's almost impossible to cut."

"What are you talking about?" the barber laughed, pointing at his own head. "I have curly hair too. Do you like my haircut?"

Joe nodded. "It looks perfect."

"So it's not impossible," the barber concluded.

"Do you cut your own hair?" John asked.

"My wife does," the barber said. "She a barber too. Pretty good, right?"

Joe hesitated. "Okay," he sighed. "I just want a trim."

"Your hair needs a lot of trimming," the barber joked. He gestured to the chair. "Hop in."

Joe sat down. The barber grabbed a metal can, sprayed a handful of shiny foam, and worked it through Joe's curls. He brushed, snipped, clipped, and shaped with two different pairs of scissors. Joe closed his eyes.

When he opened them, he gasped.

"Wow! I don't know how you did that. I have the thickest hair in the whole class."

"I know," the barber said. "I counted fifty-five thousand and six hairs on your head."

Joe nodded. "And they're all curly."

Friday, February 13, 2026

MONKEYS

This story explores Mrs. Jewls’s fear of cute children in Chapter 2 of Sideways Stories from Wayside School. Before we dive into the fan‑fiction, let’s take a quick look at what the second chapter is about.


CHAPTER 2. MRS. JEWLS — SUMMARY

A new teacher arrives on the thirtieth story of Wayside School, but she is terribly afraid of cute children. Her fears seem confirmed when she enters the classroom and sees what she believes to be a room full of monkeys. For what feels like a very long time, the students try to convince her that they are children, not monkeys. When Mrs. Jewls finally realizes the truth, she announces that they have a lot of work to do and tells them to get ready for a test.




Mrs. Jewls was both a nice teacher and a kind person. In fact, she was one of the kindest adults you could meet. Ever since she was a little girl, she had loved helping people and animals alike. In her spare time, she often searched for solutions to the problems of anyone who needed her.

One summer, while students and teachers were on vacation, Mrs. Jewls received an email from Aunt Martha. Aunt Martha ran an animal shelter in Orlando, Florida, and she needed help right away.

The next morning, Mrs. Jewls caught the first plane to Orlando, took a taxi from the airport, and arrived at Aunt Martha's house at noon. She was shocked to find her aunt still in bed, with one leg in a plaster cast.

"Aunt Martha, what happened?" Mrs. Jewls cried.

Aunt Martha moaned, sat up slowly, and rubbed her eyes. "Could you please bring me a glass of water?" she whispered. Her voice was dry and raspy. "I haven't drunk anything since I came home from the hospital."

Mrs. Jewls rushed to the kitchen and returned with a mug of water. Aunt Martha gulped it down in no time. 

"May I have another, please?" she asked.

Mrs. Jewls brought a large pitcher and set it on the bedside table. After drinking some more, Aunt Martha explained that she had broken her leg while feeding the monkeys the morning before. 

"But Aunt Martha," Mrs. Jewls exclaimed, "you're an old woman. You shouldn't be working so hard anymore!"

"I have no choice," Aunt Martha sighed. "All my caretakers left because we don't have much money."

"Then why do you keep so many animals?" Mrs. Jewls asked.

"I don't keep many animals," Aunt Martha protested. "The Animal Police came last year and took all the rhinos, the jaguars, and the hippos."

"I didn't know there were rhinos, jaguars, and hippos in America," Mrs. Jewls muttered.

"People keep all kinds of pets," Aunt Martha chuckled. "But when the animals grow too big, they abandon them. Somebody has to take care of them."

"But you said the Animals Police took them all," Mrs. Jewls said.

"They took everything except the monkeys," Aunt Martha explained. "They're very cute. I love them like my own children."

"Who looked after the monkeys while you were in the hospital?" Mrs. Jewls asked.

"Nobody," Aunt Martha admitted. "Could you go feed them for me?"

The shelter was behind the house. Aunt Martha gave Mrs. Jewls the keys and explained where the food was and exactly what she needed to do.

As soon as Mrs. Jewls opened the gate, all the monkeys began screaming like crazy, jumping, and slamming themselves against the tall fence. She worked hard to feed them, bring them water, and clean the enclosure. By the time she finished, it was already dark. She took a shower, ate a bowl of cereal, and went straight to bed.


For the next five weeks, she cared for Aunt Martha and ran the entire shelter by herself. One rainy morning, while carrying food to the monkeys, she slipped on the wet stairs and fell. When Aunt Martha looked out the back window, she saw Mrs. Jewls lying unconscious. She called an ambulance.

When Mrs. Jewls opened her eyes, sunlight was streaming through a large window. A chair and small table stood beside her bed. It was a hospital room, but it felt warm and cozy.

The door opened, and a man in a white coat stepped inside. "My name is Doctor Rossi," he said. "How are you feeling, Mrs. Jewls?"

Mrs. Jewls pointed toward the window. "It was raining this morning. How is the sun shining so brightly now?"

Dr. Rossi laughed. "That was three days ago. You've been asleep for a long time."

"Did I break my leg?" she asked.

He shook his head. "No. You were exhausted."

"Oh my goodness!" Mrs. Jewls gasped. "Who's taking care of Aunt Martha?"

"Aunt Martha has moved to a nursing home," Dr. Rossi explained. "She realized she's too old to look after the animals."

"And the monkeys?"

"They're safe," he said. "The Animal Police took them. But you need to stop worrying about everyone else and take care of yourself. You shouldn't have worked so hard alone."

"But the monkeys were so cute!" Mrs. Jewls protested.

"The problem is your brain, Mrs. Jewls," Dr. Rossi remarked. "Or maybe your heart. You're too nice. From now on, you must not teach cute children anymore. Otherwise, you might end up back in the hospital."

"But I can go back to school, can't I?" she asked.

"Of course," Dr. Rossi said. "You may teach any kind of students, except cute ones. Are we clear?"

Mrs. Jewls nodded.

But when she went to Wayside School, she learned that the children on the thirtieth story were very cute. Panic rose in her chest. She hurried up the huge staircase to the top floor, knocked on the classroom door, and stepped inside.

The room was full of monkeys.

JUMP

This is another story connected to Chapter 1 of Sideways Stories from Wayside School. Before we dive into the fan‑fiction, let’s take a quick look at the first chapter again.


CHAPTER 1. MRS. GORF — SUMMARY

Mrs. Gorf teaches the class on the thirtieth story of Wayside School, but instead of helping her students learn, she uses her strange magical powers to turn them into apples, one by one. She lines the apples up on her desk, where they sit silently, unable to do anything. When every child has been transformed and Mrs. Gorf is preparing to leave the school forever, Todd suddenly realizes how they might force her to change them back.




For several days now, Mrs. Gorf had been turning the students in her class into apples. Joe was the first kid to become an apple. John and Todd followed almost immediately, and Stephen changed soon after. He was terrified.

Every child who was transformed felt the same way. At first, they were so scared they couldn't think straight. Then the fear sank into sandness: a heavy, hopeless feeling. They were stuck, helpless, and unable to do anything about it.

Todd felt that way too. He didn't want to talk to anyone. He was frightened, upset, and miserable. His whole life had been taken away, and he had no idea how to get it back. Then one night, while the other apples were asleep, Todd noticed something strange. His whole body felt numb, like he couldn't feel anything at all, but somehow it hurt to stay still. So, he tried to move. Just a little.

POP. He made a tiny hop.

Todd froze. Then, amazed, he tried again. This time he jumped so high he landed back on the desk with a loud thud. He stayed perfectly still, afraid he'd wake the others.


But inside, he was thrilled. The apples weren't completely powerless after all. And that's when he came up with a plan.

When morning came, Todd waited for the others to wake up. As soon as they stirred, he cleared his throat.

"A-hem. Guys!"

"Oh my gosh, Todd!" Stephen screamed. "You scared me! My heart almost jumped out of my chest!"

"What chest, Stephen?" Todd muttered. "We're apples. And we need to do something about it."

"Relax, Todd," Joe whispered. "Some people are trying to sleep."

"Trying to sleep?" Todd snapped. "Wake up, Joe. We're in trouble."

"Trouble?" Joe repeated. "What kind of trouble? Stop it, Todd. No one's in trouble."

"No one's in trouble?" Todd said. "Joe, look at yourself. You're an apple."

"I know," Joe laughed. "I've been an apple for three days. Best three days of my life."

Todd stared at him. "Are you crazy? What do you mean?"

Joe yawned. "What do I mean?" He was very sleepy.

"Yes, Joe!" Todd shouted. "What do you mean by the best three days of your life?"

"Well, we don't have to study," Joe said. "No homework either. We're  on vacation."

"Oh my gosh, Joe," Todd groaned. 

"Who doesn't like vacation?" Joe asked.

"We're not on vacation!" Todd roared. "We're stuck on Mrs. Gorf's desk on the thirtieth story of Wayside School!"

"I know Todd," Joe said. "I'm not stupid."

"No one said you're stupid," Todd replied.

Joe pointed behind him. "Maurecia and Joy think I'm stupid."

"Joe's right," Maurecia admitted. "But I'll stop saying that. I promise."

"Okay, nobody's stupid," Todd proclaimed. "But that's not the problem. We have something bigger to worry about."

"Don't worry, Todd," Joe said. "I count twenty-four apples on this desk. That means only three kids are left in the classroom."

Todd blinked. "Yeah, so?"

"She'll turn them into apples today," Joe said. "Then she'll have to turn us back into children."

"No, she won't!" Todd blurted. "Mrs. Gorf hates children. She hates being a teacher too!"

Maurecia nodded. "Todd's right. Mrs. Gorf is crazy. Once everyone is an apple, she'll grab her bag and go home."

"She's a monster!" Todd declared. "She'll fly back to her lair and we'll never see her again."

"Oh my gosh!" Stephen screamed. "I don't want to be an apple forever. I'm scared!"

"We're all scared," Todd said. "But we have to act before she leaves. Nobody else knows how to wiggle their ears."

"I know how to stick out my tongue," Joe chuckled.

"Everyone can do that," Todd said. "But you can't stick your tongue now, can you? You're an apple!"

"That's why people think you're stupid, Joe," Joy muttered.

"See, Todd?" Joe complained. "She's doing it again!"

"That's because we're in trouble and you keep talking about silly things," Todd said. "We may never become children again."

"Then we're doomed," Joe whispered. "We can't do anything, can we?"

"Actually, we can," Todd said. "We can jump and hit her in the face."

"Really?" Eric Bacon asked. he loved jumping, even though he wasn't very good at it. "Who's going to do that?"

"We all are," Todd said. "I'll jump first. But one apple isn't enough."

"Of course not," Kathy agreed. "Maybe the three Erics should go next. They're all fat. That'll hurt a lot."

"How many times do I have to tell you, Kathy?" Eric Bacon shouted. "I'm the skinniest boy in class!"

Kathy laughed. "But you're the biggest apple on the desk. You're fat now, aren't you?"

"Guys, stop fighting," Todd pleaded. "We need to focus on Mrs. Gorf. She's the enemy."

"I'm ready," Stephen said. 

"I'm ready too," Joe added. "Let's do this."

"Okay," Todd said. "The sun's up. She'll be here any minute. When I bop her in the face, I want all of you to follow. Got it?"

Everyone cheered. 

ONE YEAR AGO...

This story is inspired by the introduction to Sideways Stories from Wayside School. Before we dive into the fan‑fiction, let’s take a quick look at what the introduction is about.


INTRODUCTION — SUMMARY

The introduction is very short, but it contains one unforgettable detail: Wayside School was supposed to be built horizontally, with thirty classrooms in a row. Instead, the builder accidentally constructed it vertically, creating a thirty‑story tower with one classroom on each floor. Because an elevator wasn’t part of the original plan, every student and teacher at Wayside School has to climb the stairs to reach their classroom.




It was Monday. Louis woke up early, grabbed his jacket and headed to school. As he crossed the street, he chuckled to himself. 'This is funny,' he thought. 'We only have the land where the school will be. We don't even have the school yet.'

He stopped at the hot dog stand across from the empty lot. "Good morning, Miss Mush," he said.

"Good morning, Mr. Louis," she replied. "Two hot dogs as usual?"

"Just call me Louis," he said. "And make it four today. I'm meeting the contractor this morning."

Miss Mush's hands flew as she prepared the hot dogs. "When are they finally going to build the school?"

"They were supposed to start last Tuesday," Louis sighed, watching her add mustard and ketchup. "But there were some problems with the plans."

Miss Mush handed him a warm, steamy bag. "Here you are, Louis. I hope there won't be any problems this week."

"I hope so too," Louis said, counting the hot dogs. "Wait! You gave me five instead of four. Let me pay for the extra one."

"Don't worry about it," she said with a smile. "It's on the house."

Louis paused, thinking. "You know, Miss Mush. We're looking for a lunch teacher for the new school. And you're the best cook I've ever met. Would you like to work with us?"

Miss Mush laughed. "Build the school first, Louis. If I like it, I'll definitely consider it."

Louis grinned, pulled out a hot dog, and took a big bite. "Perfect," he said, crossing the street toward the construction site.

A tall man in a hard hat stood between a crane and a bulldozer. he checked his watch as Louis approached.

"Good morning, Mr. Smith!" Louis called.

"You're late, Mr. Louis," Mr. Smith replied.

"Only five minutes," Louis said with a laugh.

Mr. Smith shook his head. "Time is money."


"You're right," Louis admitted. "And we don't have much money. Sorry I'm late. Do you want a hot dog?"

"No, thank you. I've already had breakfast."

"They're the best in town," Louis insisted. "Go on! Take one."

Mr. Smith sighed, grabbed a hot dog, and took a huge bite. "Busy day today," he said between gulps. "Since we're starting construction tomorrow, we need everything ready."

Louis scratched his head. "Yeah, about that. I'd like to discuss the school design with you."

"Again?" Mr. Smith groaned. "We've gone over the design a thousand times. Please don't tell me you want to change it."

"Well," Louis began. "I have some concerns about the layout. I think the school should be built horizontally, not vertically."

"Horizontally?" Mr. Smith blinked. "You want thirty classrooms on the same story? Why?"

"Some teachers don't like that the library, cafeteria, and administration office will be on different floors," Louis explained. "Can't we fix that?"

Mr. Smith rubbed his forehead. "I'm not sure. A horizontal building means more digging, more concrete, more everything. I'm afraid we'll have to build vertically."

"Why?"

"Because building horizontally costs more time, more materials, and more money."

"More money?" Louis yelped. "We don't want to spend too much money!"

"Exactly," Mr. Smith said. He reached into the bag and took another hot dog. "Besides, a horizontal school would leave less room for outdoor space. You don't want a tiny playground, do you?"

"We need the playground to be as big as possible," Louis agreed. "All right, Mr. Smith. We'll build vertically."

Mr. Smith shook Louis's hand. "Very good. It will be a thirty-story building with thirty classrooms: one on each floor."

Louis rubbed his chin. "Then we'll need an elevator, won't we?"

"I'm afraid we don't have enough money for that," Mr. Smith said. "Everyone will have to use the stairs."

Louis frowned. "Hmm. Miss Mush might not like that."

"Is she the owner of the school?" Mr. Smith asked. 

"No," Louis laughed. "Miss Mush will be the lunch teacher."

"If the children can climb the stairs, Miss Mush can climb the stairs too," Mr. Smith declared.

Louis nodded. "You're right."

Thursday, February 12, 2026

HUNGRY

This story is my response to the final scene of Chapter 1, when Louis eats the apple on Mrs. Gorf's desk; a moment that's both dramatic and ironic. Before we get to my fan-fiction, let's take a quick look back at Chapter 1, "Mrs. Gorf," from Louis Sachar's Sideways Stories from Wayside School.


CHAPTER 1. MRS GORF - SUMMARY

On the thirtieth story of Wayside School, Mrs. Gorf uses her strange magical powers to turn her students into apples, one by one. Louis, the yard teacher, has heard rumors that Mrs. Gorf is unusually mean. So, he climbs all the way up to investigate, unaware that she has accidentally transformed herself into an apple. When Louis enters the classroom, he notices an apple on the teacher's desk and eats it, not realizing it is Mrs. Gorf herself.





Louis was having a strange dream when the alarm clock went off. He jumped out of bed and rubbed his eyes. 'It's Friday,' he thought. 'The best day of the week.'

He went to the kitchen for breakfast but noticed the cereal box was almost empty. "I'll just drink a glass of milk," he muttered. "If I get hungry, I can always have a couple of Miss Mush's specials."

When he got to school, he suddenly remembered he hadn't washed the balls the day before. And they weren't just dusty. Most of them were coated in dirt and dried mud. So, he hauled them all down to the big bathroom in the basement and blasted them clean with a powerful hose. When he was done, he set them on the drying rack and headed to the playground to make sure everything else was in order.


Louis turned a corner and almost bumped into Miss Mush, the lunch teacher. She looked very upset. 

"Good morning, Miss Mush," he said. "Is something wrong?"

"I'm coming from the dumpster," she groaned. "I had to throw away most of the food."

Louis felt a sharp pang of hunger. "Why? What happened to it?"

"I mixed up the sugar and the salt," Miss Mush explained. "My special smelled like sweet mud. I nearly threw up when I tasted it."

Louis's stomach growled. "Then what are we going to eat for lunch?"

Miss Mush shrugged. "I don't know, Louis. I'm sorry, but there's no special today." Then she hurried up the stairs toward the cafeteria.

The bell rang, and all the children poured outside for recess, except the ones on the thirtieth floor.

"Where's Todd?" Louis wondered aloud.

He had noticed something odd: most of the students from the thirtieth story hadn't come out for recess in days. 

Just then he spotted Dameon playing tetherball. "Hey, Dameon!" Louis called. "Come here a moment. I want to ask you something."

Dameon dropped the ball and ran to the far corner of the playground.

Louis frowned. "There's definitely something strange going on."

Then he saw Jenny playing hopscotch alone. He crept behind her and whispered, "Don't be scared."

Jenny spun around. "I'm not afraid of you, Louis," she laughed.

"Good. Then maybe you can tell me what's happening in Mrs. Gorf's class."

Jenny's expression changed. "Why do you think something is happening?"

"Come on, Jenny. You can talk to me. I've heard Mrs. Gorf is pretty mean. Is she being mean to you?"

Jenny shook her head. "Nothing's happening in our class, Louis. Leave me alone."

"I know something's going on," Louis insisted. "I haven't seen most of your classmates for days. They love recess. Why aren't they out here with you?"

Jenny hesitated. "They've got work to do," she said. "Everyone's been working really hard."

"Even Todd?" Louis asked. "Where is he?"

Before she could answer, the bell rang. Jenny dashed back inside without another word.

Louis returned the balls to the sports gear room and locked the door. After a long morning of work, he felt exhausted and starving. The thought of having no special for lunch made his stomach twist. But what worried him even more was Todd and the rest of the thirtieth-floor kids.

"There's something strange here," he muttered. "I'd better check Mrs. Gorf's class again."

He had visited the thirtieth story before, and the students seemed to love Mrs. Gorf. But he still wasn't sure everything was fine. 

Louis climbed the stairs to the top of the building as fast as he could. He pushed open the classroom door without knocking.

All the children sat at their desks, but the teacher was nowhere in sight.

"Where's Mrs. Gorf?" Louis asked.

No one answered.

He scanned the room. Most of the students were busy stuffing books into their desks, then pulling them out again. Todd stared at the ceiling, chewing his lip.

Then Louis noticed a bright red apple on the teacher's desk. His stomach almost screamed.

"Boy, am I hungry," he said. "I don't think Mrs. Gorf would mind if I ate this apple."

He picked it up, shined it up on his shirt, and took a big bite.

HAIR DRIVE

The following story focuses on Joe, the main character in Chapter 3 of Sideways Stories from Wayside School . Before we dive into the fan‑fi...